Is Success the Enemy of Freedom? (Full)

by alkjash8 min read26th Oct 202058 comments

195

Social & Cultural DynamicsSocial Status
Curated

I. Parables

A. Anna is a graduate student studying p-adic quasicoherent topology. It’s a niche subfield of mathematics where Anna feels comfortable working on neat little problems with the small handful of researchers interested in this topic. Last year, Ann stumbled upon a connection between her pet problem and algebraic matroid theory, solving a big open conjecture in the matroid Langlands program. Initially, she was over the moon about the awards and the Quanta articles, but now that things have returned to normal, her advisor is pressuring her to continue working with the matroid theorists with their massive NSF grants and real-world applications. Anna hasn’t had time to think about p-adic quasicoherent topology in months.

B. Ben is one of the top Tetris players in the world, infamous for his signature move: the reverse double T-spin. Ben spent years perfecting this move, which requires lightning fast reflexes and nerves of steel, and has won dozens of tournaments on its back. Recently, Ben felt like his other Tetris skills needed work and tried to play online without using his signature move, but was greeted by a long string of losses: the Tetris servers kept matching him with the other top players in the world, who absolutely stomped him. Discouraged, Ben gave up on the endeavor and went back to practicing the reverse double T-spin.

C. Clara was just promoted to be the youngest Engineering Director at a mid-sized software startup. She quickly climbed the ranks, thanks to her amazing knowledge of all things object-oriented and her excellent communication skills. These days, she finds her schedule packed with what the company needs: back-to-back high-level strategy meetings preparing for the optics of the next product launch, instead of what she loves: rewriting whole codebases in Haskell++.

D. Deborah started her writing career as a small-time crime novelist, who split her time between a colorful cast of sleuthy protagonists. One day, her spunky children’s character Detective Dolly blew up in popularity due to a Fruit Loops advertising campaign. At the beginning of every month, Deborah tells herself she’s going to finally kill off Dolly and get to work on that grand historical romance she’s been dreaming about. At the end of every month, Deborah’s husband comes home with the mortgage bills for their expensive bayside mansion, paid for with “Dolly money,” and Deborah starts yet another Elementary School Enigma.

E. While checking his email in the wee hours of the morning, Professor Evan Evanson notices an appealing seminar announcement: “A Gentle Introduction to P-adic Quasicoherent Topology (Part the First).” Ever since being exposed to the topic in his undergraduate matroid theory class, Evan has always wanted to learn more. He arrives bright and early on the day of the seminar and finds a prime seat, but as others file into the lecture hall, he’s greeted by a mortifying realization: it’s a graduate student learning seminar, and he’s the only faculty member present. Squeezing in his embarrassment, Evan sits through the talk and learns quite a bit of fascinating new mathematics. For some reason, even though he enjoyed the experience, Evan never comes back for Part the Second.

F. Whenever Frank looks back to his college years, he remembers most fondly the day he was kicked out of the conservative school newspaper for penning a provocative piece about jailing all billionaires. Although he was a mediocre student with a medium-sized drinking problem, on that day Frank felt like a man with principles. A real American patriot in the ranks of Patrick Henry or Thomas Jefferson. After college, Frank met a girl who helped him sort himself out and get sober, and now he’s the proud owner of a small accounting firm and has two beautiful daughters Jenny and Taylor. Yesterday, arsonists set fire to the Planned Parenthood clinic across the street, and his employees have been clamoring for Frank to make a political statement. Frank almost threw caution to the wind and Tweeted #bodilyautonomy from the company account right there, but then the picture on his desk catches his eye: his wife and daughters at Taylor’s elementary school graduation. It’s hard to be a man of principles when you have something to lose.

G. Garrett is a popular radio psychologist who has been pressured by his sponsors into being the face of the yearly Breast Cancer Bike-a-thon. Unfortunately, Garrett has a dark secret: he’s never ridden a bicycle. Too embarrassed to ask anyone for help or even be seen practicing – he is a respected public figure, for god’s sake – Garrett buys a bike and sneaks to an abandoned lot to practice by himself after sunset. He thinks to himself, “how hard can it be?” Garrett shatters his ankle ten minutes into his covert practice session and has to pull out of the event. Fortunately, Garrett’s sponsors find an actual celebrity to fill in for him and breast cancer donations reach record highs.

II. Motivation

What is personal success for?

We say success opens doors. Broadens horizons. Pushes the envelope. Shatters glass ceilings.

Success sets you free.

But what if it doesn’t?

Take a good hard look at the successful people around you. Doctors too busy to see their children on weekdays. Mathematicians too brilliant in one field to switch to another. Businessmen too wealthy to avoid nightly wining and dining. Professional gamers too specialized to learn a new hero. Public figures too popular to change their minds.

Remember that time Michael Jordan took a break from basketball and played professional baseball? They said he would have made an excellent professional player given time. Jordan said baseball was his childhood dream. Even so, in just over a year Jordan was back in basketball. It is hard not to imagine what a baseball player Michael Jordan could have been, had he been less successful going in.

I think it was in college that I first noticed something wasn’t right about this picture. I spent my first semester studying and playing Go for about eight hours a day. I remember setting out a goban on the carpet of my dorm room and studying patterns in the morning as my roommate left for classes; when he returned to the room in the evening, he was surprised to see me still sitting there contemplating the flow of the stones. Because this was not the first or tenth time this had happened, he commented something like, “You must be really smart to not need to study.”

I remember being dumbstruck by that statement. It suggested that my freedom to play board games for eight hours a day was gated by my personal success, and other Harvard students would be able to live like me if only they were smarter. But you know who else can play board games for eight hours a day? Basement-dwelling high school dropouts, who are – for all their unsung virtues – definitely not smarter than Harvard students.

When I entered college, they told me a Harvard education would empower me do anything I want. The world would be my oyster. I took that message to heart in those four years – I fell in love, played every PC game that money could buy, studied programming languages and systems programming, and read more than one Russian novel. When I talked to my peers, however, I was constantly surprised at the overwhelming sameness of their ambitions. Four years later, twenty out of thirty-odd graduating seniors at our House planned to work in finance or consulting.

(Now, it could be that college really empowers these bright young scholars to realize their childhood dreams of arbitraging the yen against the kroner. But this is, as they say in the natural sciences, definitely not the null hypothesis.)

All of this would have made a teenager hate the idea of success altogether. I was not a teenager anymore, so I formulated a slightly more sophisticated answer: Regardless of how successful I become, I resolve to live like a failure.

This is a post about all the forces, real and imagined, that can make success the enemy of personal freedom. As long as these forces exist, and as long as human heart yearns for liberty, few people will ever want wholeheartedly to succeed. Were it not already reality, that is a state of affairs too depressing to contemplate.

(Just to be clear, people are plenty motivated to succeed when basic needs are at stake – to put food on the table, to get laid, to pay for the mortgage. But after those needs get met, success just doesn’t look all that great and only certain sorts of delightful weirdos keep striving. The rest of us mostly just lay back and enjoy the fruits of their labor.)

III. Factorization

I think all of the experiences in Section I can be summed up by the umbrella-term “Sunk Cost Fallacy,” but that theory is a little too low-resolution for my tastes. In this section I identify three main psychological factors of the phenomenon.

1. You rose to meet the challenge. Your peer group rose to meet you.

We are constantly sorted together with people of the same age group, at similar levels of competence, at similar stages in our careers. To keep up with the group, you have to run as fast as you can just to stay in place, as the saying goes. And if you run twice as fast as that, you just end up in a new, even harder-to-impress peer group. When your friends are all level 80, it’s dreadfully difficult to restart at level 1.

Your friends may even be sympathetic, but it rarely helps matters.

Maybe you want to try something totally new, and your friends are too invested in their pet genre to emigrate with you.

Maybe you’re excited to learn a new skill one of your hyper-competent friends is specialized in, and you ask them to coach you. Unfortunately, this turns out to be a massive mistake, because your friend only remembers how she got from level 75 to 80, and sort of assumes everything below is trivial. It’s technically possible to learn area formulas as a special case of integral calculus, but only technically.

Maybe you transition to a new role within the team, you struggle to learn a new set of tricks, and you start hating yourself for not pulling as much weight as you’re used to. You start to see a mix of pity and frustration in your teammates eyes as you drag the whole team down.

2. Yesterday, you were bad at everything, and that really sucked. Today you’re good at one thing, and you’re hanging on for dear life.

It’s hard to move out of your comfort zone when your comfort zone is one hundred square feet on top of Mount Olympus and every cardinal direction points straight off a cliff. Seems like just yesterday you stood at the base of this mountain among the rest of the mortals, craning your neck to get a peek at what it’s like up here.

Kindly god-uncle Zeus calls a special thunderstorm for your arrival. Dionysus pours you a frothy drink and shares a bawdy tale. Hephaestus personally fashions you a blade as a symbol of your newfound status. Aphrodite invites you to her parlor for a night of good old-fashioned philosophy. They all act so welcoming, so natural, so in their element, and you know you’re only up here by a stroke of pure luck.

When Hermes returns the next morning and invites you to fly with him on his winged boots to see the world, you decline graciously. Not because you don’t want to – they’re winged boots! – but because the moment you try anything out of the ordinary you’ll be found out for the impostor that you are and god-uncle Zeus will show you his not-so-kindly side and chain you to a liver-eating eagle or a boulder that only obeys the laws of gravity intermittently.

3. Success gave you something to lose.

They say beware the man with nothing to lose.

I say envy him, because he alone is free.

You fondly recall the good old days of two thousand and two when you could go online and post diatribes against religion as a “militant atheist.” In those days, you had nothing, and you were free. You were unattached. You were intellectually wealthy but financially insolvent. You could see one end of the place you call home from the other.

Now that you’ve made it big, you’d have to carefully position mirrors at the ends of three hallways to see that far. You’re attached to wonderful person(s) of amenable sexual orientation(s). You have a reputation to maintain in the ever-smaller circles that you walk. Children in your community look up to you, or so you tell yourself. And so, even though deep in your heart you still believe that only idiots believe in an old man in the sky your Twitter profile identifies you as “spiritual, yearning, exploring.”

IV. Resolution?

It seems to me we have a problem.

We are not a species known for risk-taking, so human flourishing really depends on the explicit emphasis of exploration and openness to new experience. And yet it seems that the game is set up so that the most successful people are least incentivized to explore further. That all the trying new things and pushing boundaries and calling for revolution is likely to come from those with neither the power to get it done nor the competence to do it correctly.

But it’s not a hopeless case by any means. Many of the most successful people got there precisely by valuing freedom, creativity, and exploration, and still practice these values – so far as they can – within the confines of their walled gardens. We live in an information age where getting good at things is as easy as it’s ever been. And at very least we pay lip service to healthy adages like “Stay hungry, stay foolish.”

But what does one do personally to maintain one’s freedom?

I don’t claim to have a fully general solution to this problem, but here is a rule that’s helped me in the past.

When learning something new, treat yourself like a five-year-old.

If you’ve never spoken a word of Korean in your life, it doesn’t matter if you’re a professor of English Literature. As far as learning Korean goes, you’re a five-year-old. Treat yourself like one. Make yourself a snack for memorizing the vertical vowels. Take a break after reading your first sentence and come back tomorrow. When you’re done for the day, suck your thumb while staring at the first Korean word you’ve ever learned and feel the honest pride well up in your heart.

If you’ve never washed a dish in your life, it doesn’t matter if you’re a professional chef. As far as washing dishes is concerned, you’re a five-year-old. Treat yourself like one. Make yourself a snack for figuring out how to dispense dish soap without getting it everywhere. Take a break after finishing the bowls and come back tomorrow. When you’re all done, take a moment to take in that beautiful empty sink and feel the honest pride well up in your toddler heart.

Do you see how profoundly counterproductive it would be for the Korean learner to beat herself up for not being able to converse fluently with her Asian friends after two weeks? Do you see how completely unkind it would be for the novice dishwasher to call himself a useless piece of shit for not being able to execute the most basic of adult tasks?

Be kind to yourself and adjust your expectations to reality. When learning something new, treat yourself like a five-year-old.

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Slack enables exploration.

Exploration enables exploitation.

Exploitation destroys slack.

Wow, this comment alone makes writing the entire post worth it.

Interesting, this also shows up in business as "the innovators dilemma".  Small businesses are willing to explore riskier technologies that are only profitable to smaller segments (exploration).  Eventually, they can exploit this and find ways to make that technology palatable to larger audiences (exploitation).  As they get bigger, they can't justify going after technologies with small audiences because it doesn't help their bottom line (slack destroyed).

 

Eventually, they get replaced by the next firm who went through the loop.

Am I being exploited by other pressures, or am I the one exploiting a single (good) opportunity to the cost of my slack?

At first, you are voluntarily exploiting the good opportunity because... well, because the rewards are good. You get lots of money and/or respect. And you can keep getting it, if you continue this line of work.

Then the hedonistic treadmill makes you less happy again, but the work continues consuming your time.

Even worse, the situation may be unsustainable, because your existing skills may become obsolete, and you have no time to get new ones.

One option is to wait until the bitter end, or rather until the moment the skill is still profitable but only a little, so the opportunity cost of learning a new skill is now sufficiently low. How exactly this works out depends on the shape of the skill profitability curve. (I heard that people coding in Cobol still make lots of money, despite the shrinking market for their skill, because the supply of their skill shrinks even faster.)

Second option is to predict this moment, and decide to jump ship in advance. You give up the tail of the old curve, but you get to ride the peak of the new one. There is a certain risk involved: you know how good you are at the old skill, but you can only guess how good you will be at the new one.

Third option is to resist the pressure and decide that no matter what happens, you will keep spending e.g. 10% of your time learning and practicing new things (specifically: new things unrelated to your currently most profitable skill; as opposed to deepening the skill or learning adjacent skills). Note: I didn't put this option last to suggest that it is the best one. It really depends. In case of the Cobol developer who is five years away from retirement, spending 10% of time learning unrelated technologies is probably a waste of time. Also, it depends on what is intrinsically interesting for you: maybe you still enjoy the old skill only not as much as before, or maybe it turned into a chore and you hate it but you need the money.

In some sense, this is a paradox of (Pareto-) optimal behavior. If you frame it as "this is the best you could do" it sounds great, but if you frame it as "any change will only make things worse" it sounds ominous. Yet it is the same thing.

I read it as the latter.

This feels to me like the result of very specific/narrow criteria for "success" and personal ambition, which haven't applied to most people I hang out with. (Except for becoming more risk-averse about things that have high tail risk or might destabilize one's life once you have kids, which seems very reasonable to me and a worthwhile tradeoff for the category of person who values having children a lot.) In particular, the nurses I worked with didn't come off to me as feeling constrained-by-success in this way. 

I currently both feel pleased with my life trajectory, and also like I have a lot of freedom to go in a completely different direction this year if I want. My original undergraduate degree and job were in ICU nursing, I later pivoted to nonprofit operations & finance work, and then left that to work on writing a novel. I'm considering whether I want to continue with writing or do a programming or data science bootcamp (both of which I have minimal background in), and both of these feel like very viable options. It's...honestly kind of hard for me to imagine what it would be like to be reluctant to start learning a new skill I know very little about, and I'm definitely not worried about being judged by my peer group for it. I do think I'm pretty lucky in what peer group I have, and also in having a background that doesn't lend itself to people having those expectations of me. 

It's...honestly kind of hard for me to imagine what it would be like to be reluctant to start learning a new skill I know very little about, and I'm definitely not worried about being judged by my peer group for it.

Curious if you've had anything like the following experiences: most Starcraft players I know only play the one race they picked up in the first couple weeks of play, and finds switching races difficult psychologically (more so than learning the game fresh). Most DOTA players I know only play one role (or two similar ones) out of five and find picking up other roles difficult.

(One of) the feature(s) I'm pointing out is that nobody has to be mean or judge you for you to feel bad for switching...because you start losing a lot.

I suspect with Starcraft there might be the issue of... conflicting intuitions/muscle-memories? Muscle-memory mix-ups sometimes happen when you learn 2 things that have similar cues, and avoiding those mistakes can cost you in reaction-time.

If there's a batch of early-game keystrokes you need to drill into muscle-memory to begin a Zerg play, and a different batch of keystrokes for a Protoss play, having them mash-up on you under stress is a setback on both skillsets.

A more glaring example: learning to ride left-right reversed bikes is likely to disrupt your ability to do regular bike-riding for some time.

I'd have suspected that for things as different as baseball and basketball, this probably wouldn't apply as much. (And if you commit HARD to the switch, it's probably not as big of an issue; just a hill to climb initially, then smooth sailing for a while, but some transition-time needed when you switch back.)

...but the Michael Jordan article actually mentions that there was at least one case where MJ followed basketball intuitions to run more bases than anyone else thought was optimal. So the "misapplied cross-field intuitions" disadvantage might still have a role here.

(Something something generalizability vs hyperspecialization trade-off)

Uh, I haven't strongly had that experience, I think mainly because my life hasn't contained that much in the way of competitive games with very legible winning metrics? One of the "switching skills" cases I'm thinking of is when I was hired for an operations role, and most of my previous experience was in volunteer event logistics, but for a bunch of contingent reasons I ended up instead focusing on finance work (largely because the person previously doing that was now spending most of their time on other work, and the team already had a person with a lot of skill at event-running.) This did mean I was going from an area where I felt comfortable and had a sense of mastery to one where I felt very inexperienced and sometimes overwhelmed, and made more mistakes as a result, but I don't think it parsed to me or anyone else on the team as "losing"? There was work that needed doing, it was my comparative advantage if not absolute advantage, and me doing it imperfectly was much better than it not happening. 

I related hard to the dota thing because that happened to me. After 5k hours spent honing one role... I couldn't switch. Nobody judged me but I hate losing and that was enough to sour it.

I play StarCraft 1 month a year, and it's true, I stick with Protoss. Although now that you mention it, next time I play I'll play Terran to see what happens...

But I also learn bits of languages frequently and maintain 2 foreign languages, and although there is always some switching cost with languages, it's not competitive and so the costs to switching are low.

This feels to me like the result of very specific/narrow criteria for "success" and personal ambition

Agreed. I think it would be great to factor the term "success" into more descriptive and specific terms. But at the same time, for the purpose of this post I think the usage of the word is clear and there isn't really a need to disambiguate.

At least for the purpose of communicating. Maybe it's worth it for the purpose of nudging society towards thinking about success differently.

Something about this hit me pretty hard in a way that other similar things hadn't. 

I'm reminded of this SMBC about how you can have multiple lifetimes (it takes 7 years to master something, that's several different things you could be great at over the course of your life, which'd shape your life in very different ways). But, people tend to get stuck in the thing they know.

In my case...

...hmm... I feel some kind of creeping horror at growing stagnant. But I also feel something like "don't have the time to actually learn new things from the ground up." Or, I know that I'm pretty-okay at the stuff I'm pretty okay at. I could learn totally new skills, but, it'd be years before I found out if I was especially good at them and whether they were worth it.

I noticed further that part of the problem is I don't currently have what I'd call mastery at any particular skill. The only thing I'm remotely close to "world class" at is "rational ritual design", which is mostly a fact about the rest of the civilization being inadequate. 

Huh, I recall a couple years ago I became anxious about becoming a has-been who's only ever done one cool thing, and then defined myself by that thing. And started trying to ask myself "okay, who is Raemon if he's not the Secular Solstice guy?". That motivated me to learning harder into "be good at epistemics" and "be good at programming."

And I guess that was... 3-4 years ago, and maybe it's just okay if since then I've just been sort of middling at those things. I don't currently feel on track to be great at them within another 4 years. But, remember, this makes me feel more reasonable about not currently feeling great about diving into Some Other New Skill.

I really like the pattern you used of starting with parables and following up with your motivation for writing the post.

I think the parables did a great job of quickly (and entertainingly) giving you an idea of what the post is about via "show don't tell" and "concrete before abstract". In particular, I like that you provided a handful of them. One or two might have been a little ambiguous but having a handful makes it pretty clear. When I write this out this all sounds like obvious writing 101 sort of stuff, but in my experience writing and my experience reading the writing of other people, it just always seems to prove more way more difficult than it seems.

I also really like the idea of mentioning your personal motivation/inspiration for writing the post. I'm having trouble putting my finger on why that's useful to have, but I have a pretty strong sense that it is useful to have (most of the time).

(I notice that this comment sounds a bit like an instructor grading an essay. I don't mean for it to come across that way, I just really admired those things about your writing.)

Thanks for this! It is hard to overstate how desperately I cling to every piece of praise I ever receive, especially when it comes to writing. You didn't come off condescending at all.

I have some areas of artistic expertise where everyone around me is kind of like a level 10 and I'm a level 80. When I try skills near to it, I'm immediately a level 25, and so I actually feel pretty good exploring them. Note that these are not the core skills that my reputation and social status rest on.

I can think of many examples where I think this sort of dynamic happened in the world. I feel some impulse to not name them all because it's psychologizing others a bit. But I'll say one that I thought of lately was wondering why Nate Silver didn't do any forecasting around the pandemic, and this sort of answer was what I settled on.

You say you resolved to live life like a failure, which I like. I have something like this, but those words don't quite resonate with me. Paul Graham says to try to feel like a noob often, and he has the great line "the more of a noob you are locally, the less of a noob you are globally", which I also like.

This reminds me of Seneca.

Your modern parables give a better frame for some of his advises:

"Set aside a certain number of days, during which you shall be content with the scantiest and cheapest fare, with coarse and rough dress, saying to yourself the while: “Is this the condition that I feared?”"

All of this would have made a teenager hate the idea of success altogether. I was not a teenager anymore, so I formulated a slightly more sophisticated answer: Regardless of how successful I become, I resolve to live like a failure.

I strong upvoted for this line

If I were to come up with a Clever Title for some of this, I might call it The Trap of the Local Maxima. 

I did childcare and disability care in college, because it was a better option than being a cashier or something. Then I graduated and it was a recession, but I could use my childcare experience to get nanny jobs. And so on, and so on. 

Now I have about 15 years of childcare experience. It is REALLY EASY for me to get GOOD PAYING nanny jobs. I can literally go on to a website, send out 5-10 applications to what I think are the best jobs there, and be working within a week. 

Every now and then I try to do something else, but it is harder to find other types of jobs given my resume, and when I do the job is usually harder than nannying, and pays less. (I was recently an Office Manager, which had expectations I couldn't live up to, and paid less than nannying. Now I do some Virtual Assistant work that is mostly writing / social media which is nice and easy, and a similar amount of pay per hour, but not as many hours per day)

I don't even LIKE being a nanny. I never CHOSE it as a career. I don't PARTICULARLY like children (not in the way most people who choose childcare do). Kids are easy, but my people-skills are mediocre when dealing with e.g. parents or other nannies. 

I tell myself someday I will semi-retire and be a dog walker.

This is a huge ugh field for me that I have been meaning to explore for a long time. I think the reason why I never actually explore it is because it feels like a very deep rabbit hole that is intimidating to start going down.

When I was a sophomore in college, after reading How to Start a Startup, I decided that I wanted to start startups, make a ton of money, and then use that money to make the world a better place. And I wanted to pursue these goals really, really hard. My mindset was:

I care about achieving them so yes, I'm going to make an actual effort to achieve them. But if I fail, then the fallback plan is still good. It'd be reaching for the stars but landing on the clouds. Eg. having a cushy life as a programmer that would provide me with way more money than I'd know what to do with, the ability to retire early, as an upper-middle class person in a first world country in the 21st century, with a million interests that I could spend time pursuing, etc.

Fast forward eight years, I haven't really had any success and my happiness set point has changed. Achieving my goals makes me feel normal. Call it a 5/10. Not achieving my goals, and feeling "behind", which is where I spend most of my time, makes me feel anxious. Call it a 2/10. It shouldn't be like that though. I should feel like a 7/10 when I don't achieve them and a 10/10 when I do.

One path forward is to fix this bug in my brain. But is that possible? Well, "possible" is a very low bar. I think a more useful question is whether it is plausible. In exploring that question, I look around at successful people, similar to what you've done in this post, and I find that they all have similar problems. Their set point changes, it feels normal when they achieve their goals, upsetting when they don't, and that their default state is "feeling behind" and trying to "keep up". It doesn't feel like there are too many exceptions to this.

I'm not inside other people's heads so I can't say for sure, but if it's true, well, I think it is a pretty big blow to the idea that being ambitious makes sense. Not a fatal blow — maybe when you go under the hood and look at the gears it turns out that this is a fixable problem — but still a big one. Another thought: maybe some goals are important enough that they're worth pursuing even if doing so won't make you happy.

Here's another angle at the same bug, I think. I have a gut intuition that goes like this:

Real success is a Pareto improvement.

There should be some direction you can move from where you are now, where you literally get more (or at least not less) of every single thing you want. Whatever direction that is should be what we call "success" in our heads. (And since social approval is quite important to most people this definition actually lines up decently well with the conventional definition anyway.) So when people say things like "I'm happy where I am now and wouldn't want to be more successful/ambitious," or when people do striving-like stuff and ostensibly make progress but then somehow end up worse off, or when people say things like "I plan to do so-and-so which will improve my life, but I'm just not there yet" instead of diving straight in ... my gut translates these actions as "I don't want what I want" and just gets very very confused and cynical.

I definitely see the logic to this. However, here is where it goes wrong for me, and where I moderately strongly suspect it would/does go wrong for others too.

I can and do try to tell myself to just focus on the process and on making forward progress. To be happy and content with this, rather than focused on the destination. But at the end of the day, the destination is still in my head. I can't get it out of my head. And I care a lot about it. And I'm not capable of the self-deception or compartmentalization it would take to simultaneously care about the destination while also not caring about it and instead only caring about the process. So when I try to just focus on the process, my mind doesn't cooperate and continues to care about the destination.

I also recognize this feeling of "You have not done enough" or worse "This goal was meaningless in hindsight". It's probably very instrumental, pushing us and our genes to ever greater heights.

So should we lean in to it? Accepting happiness is forever lost behind some horizon? You will just walk around with this internal nagging feeling.

Or should we fix this bug as you say, but risk stagnation? One way may be to become a full-time meditating monk. Then you may have a chance to turn your wetware into a personal nirvana untill you pop out of existence. But that feels meaningless as well.

I'm trying to find a blend; take the edge off the suffering while moving forward.

The freedom to legitimately make a wider range of decisions is possible to expand while increasing success in some cases. I see most software engineers go down a path of increasing their financial obligations along with their incomes. I have tried to limit this over time, and instead, I take about 2/5 of my time off long-term. As a 32 year old, I've taken multi-year breaks from employment and lots of multi-month breaks. Funny enough, in this time I've gained niche software engineering skills in things that I would probably not have been able to acquire at work, which has opened up a variety of interesting jobs that I don't think would have been accessible via a path of continuous employment. For me it has been the opposite of the fear that most people are inclined to believe where the next employer will see a "resume gap" and be uninterested. In my time off of work, I have been able to build many personal relationships that would not have been accessible if I were working 40 hours per week continuously with a measly 4 weeks off per year. More relationships => more opportunities. More time for relationships => higher quality relationships => higher quality opportunities. This lets me work even less over time, and usually for 3 or 4 days per week when something interesting crosses my path. The labor market is extremely inefficient and it can often be exploited heavily to gain personal freedom and success simultaneously.

This is fascinating, I've not heard of a single SWE who takes many multi-month breaks. If you don't mind sharing, I'd love to hear more details on how you manage this. How are you able to negotiate longer breaks with your employer(s), or do you have to keep jumping ship? I would think that it's extremely expensive (especially with how equity vests), exhausting, and inefficient to be quitting jobs and starting new ones in order to take breaks shorter than say a year. 

The labor market is extremely inefficient and it can often be exploited heavily to gain personal freedom and success simultaneously.

Can you say more about this?

Humans, by default, define success in part by social approval, and status is a zero sum game. If instead your goal is to live a life that you find meaningful, in a community you choose, and you manage to genuinely not care what the rest of society thinks of that, you end up with a lot more options. I may need lots of prestige to become a tenured professor at a top university, and getting that prestige is very costly, so yes, if that's the kind of success you want, you're going to pay in giving up other options. 

Could Michael Jordan, instead of trying to become a professional baseball player, have retired from pro sports and founded a recreational league for former pro athletes interested in playing a wider range of sports? No sponsorships, no TV deals, no salaries, just playing for fun in a still-high-level environment? I don't see who could have stopped him, he had enough money to do it and I doubt he would lack for interested participants. I've certainly heard enough stories of pro athletes who lose all joy they ever took in their primary sport. 

Your Tetris player could have created a pseudonym and a second account where he never used his signature move, then later start incorporating the signature move into the second account's play. Or just not care if his play suffered for a while, the surprise everyone with a comeback once he has two well-practiced signature moves. Who doesn't love a comeback story? And then if he does it again, people won't be surprised by it as much.

Deborah can tell her husband how unhappy she is, and if he worth having as a partner he'll understand. They'll sell the expensive house, live somewhere nice but modest, and she can write whatever she likes.

So yes: society lies to everyone about what "success" is and means. I'm a Harvard grad myself, and while I didn't know this until several years in, most of what you get by going to a place like that is the opportunity to gain status, to form certain kinds of connections that are helpful for playing certain social games, and to be seen as a certain kind of person when it's useful to do so. The math, physics, comp sci, and everything else you learn are the same there are at hundreds of other good schools.

Also, even in high status environments, it is sometimes possible to cultivate a reputation for being eclectic in various ways, but you have to be savvy enough to pull it off while still clearly "fitting in" enough to be worth keeping around. Flouting some norms can be an act of claiming high status, or it can be done in such a way it's seen as adding more diverse but useful viewpoints.  You can be the person people go to with problems so hard the conventional approaches aren't working. Anna can rightly claim she was able to solve a major problem because of the other niches she studied, and if that doesn't help she can look for a new advisor at the cost of a slower path to graduation. Or, she can leave academia (like most PhDs and PhD students do), live a life that provides her free time, and study anything she wants, publishing anything useful along the way. Does her field of pure math require full-time work and lots of grant funding, or just basic, widely available tools and her brain?

I certainly agree that all the things you suggest to maintain one's freedom are technically possible. It is technically possible for Michael Jordan to abandon the entire status-oriented psychological machinery he built throughout his life to become the GOAT and play baseball in a recreational league. It is technically possible to simply stop caring about an entire dimension of human experience and set yourself free from society's notion of success. 

This post is a set of observations about how succeeding a second time in a different area is often harder than succeeding the first time. Of course it is still not impossible, and indeed it happens all the time, but significant extra effort is required that was not required the first time. This seems to me surprising and counterintuitive, because my initial model of such things was that success multiple times should only get easier and easier, since "gitting gud" is a cluster of highly generalizable skills.

Hmm, it seems maybe relevant that I don't think of my various skill-acquiring periods in the past as about "success"? Or maybe that the thing my brain parses internally as success isn't very defined by what society considers to be winning. When I moved from ICU nursing to operations work, it did involve going from somewhere I was acknowledged by my colleagues to be pretty good at and where I felt a lot of mastery, to somewhere where I was much more often making mistakes and getting criticism for them, and this was sometimes frustrating and hard. Still, my overall sense was still one where learning to be a good nurse gave me a ton of generalizable skills that transferred to ops and meant I could skill up a lot faster there. Possibly it helps that I picked nursing for reasons unrelated to its prestige, and in fact got a bunch of flak from people (including people in the rationalist community) about choosing this field.

Aside: the experience I've had that feels the most to my S1 like having "made it in life", is participating in glowfic, a very niche online collaborative-rp-writing community. Writing fiction and having a couple of dozen people as avid fans of it is utterly maxing out my monkey brain's metric for feeling high-status. I do think it'll be a bit of an adjustment going back to full-time work of one sort or another (I've been doing a lot of this as a hobby while recovering from a serious medical issue, but will at some point be recovered enough to be productive on other things and will cut back substantially.) Possibly because it's so niche and only involves a subset of my social circle, though, I don't expect it to make learning different new skills feel like "losing." 

Human capability usually peaks around the age of 25; that's about how old Einstein was during his "miracle year".  After that, everything gets gradually harder.  For a while, it's hardly noticeable unless you enter a new, hyper-competitive environment.  Later on people rely on built up advantages to stay competitive.  Eventually time makes fools of us all.

Exactly. My point is that "succeeded a second time" isn't a question of skill, it's a question of societal status assignment mechanisms and the value we place on status. It's true, I can't claim any given individual can actually turn off the parts of their mind that care about status, but some people do happen to care less about that, and do go on to have multiple successes. Those kinds of figures tend to be somewhat polarizing personalities, but after the second time there is less resistance to the third. People expect it more of them.

I am not sure if this would solve the issue for you, but I try to make passive income towards not being dependent on work, so that I have the freedom to do what I want. But I am really not sure this would solve it because I think you pointed out that even wealth can be a limitation. It depends how much time you spend to maintain in it and how successful you are with it

I think the real reason is that exploration is a stage in life; it naturally ends with parenthood.  Our goal in youth is to explore the world until we find a way to succeed.  In adulthood, our goal is to maintain a stable environment so that our children and students can safely explore.

For a person with an average income (relative to their peer group), you are right. Keeping a competitive job and taking care of your family takes almost all your energy and time, and you can't take risks.

However, if you have enough money to retire early, you can take care of your kids and keep exploring the world (while the kids are at school). You can even explore some things together, if your kids are interested at doing something you never did before.

In families that can live on one income, the other partner is similarly free to explore the world (while the kids are at school, or with them). I know a stay-at-home mom who started a successful online business.

Success raises the degree to which you can explore without wrecking the stable environment you've built; it also raises the bar for what you consider exploration.  A waiter with two kids might dream of backpacking across Mexico but be too tied down to do it; an executive could easily afford a family vacation in Mexico but would dream of something larger that he's too tied down to do (start his own company, learn to code well, become a doctor, whatever).

Curated. This is an idea I've thought about a little before, but this post says everything so cleanly and clearly, and helped me think about it in ways I had not before. The idea carries with me stronger for reading this post.

And the writing is great. I normally emphasize readability in curation notices, but here I feel like I also want to call it 'poetic'. Whatever.

(And yep, I see the irony in curating it, but the irony does not seem to me worth it to avoid. If Alkjash disagrees I will obey his preferences of course.)

I think learning about xrisk has this kind of “binding you” quality. Once you know about it and you care enough, you can’t look away.

fwiw I've noticed that my feelings about x-risk have started to loosen recently, though it's probably because some of my metaphysics are shifting

Thats interesting. Can you elaborate more? 

It's a big topic and I don't have a great articulation for it yet. 

Some scattered points:

  • Generally higher model uncertainty than I used to have
  • Idealism now seems as plausible as materialism
  • Panpsychism seems plausible / not-crazy, and consciousness matters a lot
  • The many-worlds interpretation seems plausible. If physics is many-worlds, we may not be able to ever escape from ethical parochialism
  • Not about metaphysics, but I've been growing less confused about my motivations such that ethical considerations no longer feel as fraught. (I used to identify my ethics with my view of my self-worth such that acting ethically seemed super important)

p-adic quasicoherent topology

I'd love to chat with you sometime about this. I have scheduled an appointment on Calendly (link provided for those who haven't used it before)

Also: quick question: is there actually a connection between p-adic quasicoherent topology and matroid theory, or is that just for narrative? (I don't know much about matroids)

I may be wrong, but based on the matroid reference I believe the inspiration for the example is a Quanta article about June Huh, who solved the Rota conjecture.

All the details in the parables section are strictly apocryphal, though there are only a small number of Quanta articles that this story is generalizing from. 

From what I know of June Huh in particular he is working on exactly what he wants to be working on.

Looking forward to it! To be clear that isn't a real branch of math (afaik).

To be clear that isn't a real branch of math (afaik)

I figured there was a decent probability of that being the case. I still anticipate it will be a good icebreaker

This resonated a lot with me! (And I'm far from as successful as I would 'like' to be - or would I??? :angst:)

Speculative and fuzzy comparison-drawing

I was reminded, I'm not sure exactly why, of this interesting entry I recently came across (I recall I was led there by a link buried in a comment in Slate Star Codex somewhere...) https://plato.stanford.edu/entries/capability-approach/

While I wouldn't necessarily endorse all of it, it's an interesting read. As I understand it, the capability approach advocates a certain way of drawing lines in practical policy-making. Its emphases are on

  • ‘functionings’ ('beings' and 'doings')

    various states of human beings and activities that a person can undertake

    example beings: ...being well-nourished, being undernourished, being housed in a pleasantly warm but not excessively hot house, being educated, being illiterate, being part of a supportive social network, being part of a criminal network, and being depressed

    example doings: ...travelling, caring for a child, voting in an election, taking part in a debate, taking drugs, killing animals, eating animals, consuming lots of fuel in order to heat one's house, and donating money to charity

  • 'capabilities'

    a person's real freedoms or opportunities to achieve functionings

Here's a passage which we can hold alongside the premise of the original post

The ends of well-being freedom, justice, and development should be conceptualized in terms of people's capabilities. Moreover, what is relevant is not only which opportunities are open to me each by themselves, hence in a piecemeal way, but rather which combinations or sets of potential functionings are open to me.

For example, suppose I am a low-skilled poor single parent who lives in a society without decent social provisions. Take the following functionings: (1) to hold a job...to properly feed myself and my family; (2) to care for my children at home and give them all the attention, care and supervision they need. ... (1) and (2) are opportunities open to me, but they are not both together open to me... forced to make some hard, perhaps even tragic choices between two functionings which both reflect basic needs and basic moral duties?

[emphases in source]

Although that summary of the approach and the excerpt I've copied don't articulate this 'success as enemy of freedom' idea, I wonder if it would be helpful to consider the idea with the lens of the capability approach? There's a certain paradoxical symmetry of the examples, which I think is what the OP is drawing attention to. The challenge would be to draw out whether the mechanism is societal or part of human nature or some combination thereof or (...) and what measures we might take (individually or collectively) to mitigate it!

I relate very much to your old roommate who commented on your studying Go and attributing it to your intelligence. While I have always imagined myself living in a small wooden cottage with plenty of time to pursue my interests, I find it very difficult to evaluate a freedom/success trade-off while still in university. Even though I could make the case that I will most likely live more-than-comfortably as a data-scientist no matter how well I perform at the next examination, I still can't shake the feeling that I should be pushing myself to the limit. I feel as if the "fog-of-war" for determining future freedom is too thick, but I realize that I haven't actually tried to make a plan.

So here's the first outline of a "wooden cottage" plan:

  1. Graduate with a masters degree to ensure employability
  2. Acquire units of purchasing power in local currency
  3. Pay off debts, build a heap of gold coins under a mountain
  4. Scare off dwarves and a hobbit
  5. ??? 

I'll figure the rest out later, but thank you for planting the seed in my mind.

I enjoyed this post, although I don't necessarily think sucess is essentially what is taking our freedom away. Firstly, what do you understand by sucess? I believe it might be highly subjective. 

Do you think success is economical, professional, intellectual...? Is it a static goal or is it a journey? That changes how it influences your freedom. In essence, the definition and meaning that you give to your own life will change very much I free do you feel. 

I don't think that success itself is the reason of constrained freedom, I believe that "identity" is. I have always thought that defining one self translates to limiting what we could be. When we are five years old we could be anything! All we learn is new, exciting and you don't really have a sense of identity developed enough. You could be really good at that and that is intrisically exciting! When we are young we have a curious and ambitious mind not yet defined (hence this sense of freedom: nothing in your life is yet defined). However, with age, external constraints and the natural path of life limits your options. For example, specialised careers or studies, creating a family or mastering any skill...   All of that defines what you are in a very strong manner (to society and to yourself) and that can definitely limit your freedom. 

I believe that as we age and we take important decisions in our lifes, our freedom is affected by the loss of possibilities. However, it all depends how you perceive yourself, how much do you want to organise and box your identity and what are you after in this life. 

Do you think success is economical, professional, intellectual...? Is it a static goal or is it a journey? That changes how it influences your freedom. In essence, the definition and meaning that you give to your own life will change very much I free do you feel. 

In my writing I err on the side of using simple words in the hopes that the charitable reader interprets it in whatever way it makes the most sense. Here I think I define "success" as "psychological success" = whatever makes you currently feel successful.

I don't think that success itself is the reason of constrained freedom, I believe that "identity" is.

I definitely agree that strong attachment to identity is one of the big factors that constrain freedom, however I disagree with reducing this entire phenomenon to one mechanism. In my personal experience whenever I break what seems to me to be the biggest barrier, e.g. "identity", to my freedom, I usually make progress for a period of time only to find another, entirely different barrier, in my way. To use a video game analogy, this is a final boss with multiple stages and "identity" is probably the first stage that most people get stuck on.

It seems like the shape of reality is itself bent in such a way to constrain our freedom, independent of whatever psychological attachments we have internally that only make matters worse.

I agree that success has multiple dimensions, and I think "identity" is a plausible explanation for what's going on here.

But also, previously when I had asked "do children lose childlike curiosity?", an answer that came back was "are we even confident that 'childlike curiosity' is a thing?". This comment reminded me that I'd still like someone to look into that in more detail.

Strong upvote. Success doesn't limit us. Success changes us. It is what we become that limits us.

Live free of attachment and you will always be free.

I don't really agree with the concepts used here, nor with the conclusion.

The basic idea behind this article is that an increase in responsibility & standards in one field limits one to that field, this is simply untrue, or at least often not true.

For example, an academic might indeed get piegenholed into studying the niche they got good at, but that is only true until tenure.

A financial advisor might indeed be stuck doing boring backhanded deals and attending highhigh-class class NY bars to get access to the best dark polls, but that's only until they have enough money to quit working.

***

In part, the problems you outline are ones regarding how people put less value on freedom as they progress through life. But this is only natural and happens regardless of success levels.

However, given a change in value is possible, transitioning from a field to another should be easier, not harder, with success.

***

So the conclusion of putting on baby wheels when learning something new is not one I'd agree with. Indeed, I'd rather push myself much harder than I would push young me, since my previous experience and knowledge is likely to give me a better starting point for many endevours, at least for most of those I could potentially find interesting.

Even if it wouldn't, the "don't push yourself too hard" is simply a counter-biasing tool, useful only for saying "Hey, remember that X thing you are really good at, well, Y is completely unrelated to that, so expect to be mediocre at Y and take it slow".

I have changed occupations thrice - from a PhD student (dropped out) to lab technician (in a different lab, for children), from LT to bookshop cashier/..., from BC to the-one-who-proofreads-articles-and-stuff in a lesser research journal. I kind of expect to switch at least once more, to a librarian or postman.

All of it revolves around the need to be home for the kid, and around hating some aspects of the job. (The lack of science; the late hours; the cold; and currently, the need to be reputation-wise.) And there was freedom in every thing I've done, although not exactly freedom to do what I wanted to do. Just - freedom to see the world. I think it should not be underestimated.

Valleys of bad rationality and Reason as memetic immune disorder come to mind after reading this. I think framing it these ways is useful.

Pursuing success is... well... good, we can say. But there are some serious dangers along that road. It makes me think that mental health maintenance/self-care should be an important component of the art of rationality.

I want to keep being successful despite the costs to my freedom, but that's because I view my success as a service (hence I get paid for it), not as a source of my own happiness. Esse quam videri.

And freedom is a terrible master. I was far more free from college to college + 3 years, but freedom is something you spend. It's a currency which you exchange for some type of life. Now I have very little slack, but I have an endless supply of good places to devote my energy. And that's freedom to do good, the highest form of freedom.